Hiyama coupling sahifasining manbasini koʻrish

'''Xiyama birikmasi''' - bu uglerod-uglerod bog'larini (C-C aloqalari) hosil qilish uchun [[Organik kimyo|organik kimyoda]] ishlatiladigan organosilanlarning organik galoidlar bilan [[palladiy]] katalizli o'zaro bog'lanish reaksiyasi. Ushbu reaksiya 1988-yilda Tamejiro Xiyama va Yasuo Xatanaka tomonidan kimyoviy va regioselektivlik bilan sintetik ravishda uglerod-uglerod aloqalarini shakllantirish usuli sifatida kashf etilgan<ref name="Hiyama Discovery">{{jurnal manbasi|last=Hatanaka, Y.|last2=Hiyama, T.|journal=[[Journal of Organic Chemistry]]|title=Cross-coupling of organosilanes with organic halides mediated by a palladium catalyst and tris(diethylamino)sulfonium difluorotrimethylsilicate|year=1988|volume=53|issue=4|pages=918–920|doi=10.1021/jo00239a056}}</ref>. Xiyama birlashmasi turli xil tabiiy mahsulotlarni sintez qilish uchun qo'llanilgan<ref name="Denmark Review">{{jurnal manbasi|last=Denmark, S. E.|last2=Regens, C. S.|journal=[[Accounts of Chemical Research]]|title=Palladium-Catalyzed Cross-Coupling Reactions of Organosilanols and Their Salts: Practical Alternatives to Boron- and Tin-Based Methods|url=https://archive.org/details/sim_accounts-of-chemical-research_2008-11_41_11/page/1486|year=2008|volume=41|issue=11|pages=1486–1499|doi=10.1021/ar800037p|pmid=18681465|pmc=2648401}}</ref>.

: <math chem="" title="The General Scheme for the Hiyama Coupling">\begin{matrix}{}\\
\ce{{R-SiR''_3} + R'-X ->[\mathrm{F^-}][\text{Pd cat.}] R-R'}
\end{matrix}</math>
:* <chem>R</chem>: aryl, alkenyl or alkynyl
:* <chem>R'</chem>: aryl, alkenyl, alkynyl or alkyl
:* <chem>R''</chem>: Cl, F or alkyl
:* <chem>X</chem>: Cl, Br, I or OTf

== Reaksiya tarixi ==
Xiyama muftasi boshqa organometalik reagentlar bilan bog'liq muammolarga qarshi kurashish uchun ishlab chiqilgan. Organosilikonning dastlabki reaktivligi aslida Xiyama tomonidan birinchi marta xabar qilinmagan, chunki Kumada quyida ko'rsatilgan organoflorosilikatlar<ref name="Kumada Fluorate">{{Citation|last=Yoshida, J.|last2=Tamao, K.|last3=Yamamoto, H.|last4=Kakui, T.|last5=Uchida, T.|last6=Kumada, M.|journal=[[Organometallics]]|title=Organofluorosilicates in organic synthesis. 14. Carbon-carbon bond formation promoted by palladium salts|year=1982|volume=1|issue=3|pages=542–549|doi=10.1021/om00063a025}}</ref> yordamida ulanish reaksiyasini xabar qilgan. Organosilanlar keyinchalik Xiyama tomonidan ftorid manbai tomonidan faollashtirilganda reaktivlikka ega ekanligini aniqladi<ref name="fluoride activation">{{Citation|last=Hiyama, T.|last2=Obayashi, M.|last3=Mori, I.|last4=Nozaki, H.|journal=[[The Journal of Organic Chemistry]]|title=Generation of metal-free silyl anions from disilanes and fluoride catalyst. Synthetic reactions with aldehydes and 1,3-dienes|year=1983|volume=48|issue=6|pages=912–914|doi=10.1021/jo00154a043}}</ref><ref name="Hiyama JOC">{{Citation|last=Fujita, M.|last2=Hiyama, T.|journal=[[The Journal of Organic Chemistry]]|title=Erythro-directive reduction of.alpha.-substituted alkanones by means of hydrosilanes in acidic media|year=1988|volume=53|issue=23|pages=5415–5421|doi=10.1021/jo00258a004}}</ref>. Ushbu reaktivlik palladiy tuzi bilan birlashganda, organik halid kabi elektrofil [[uglerod]] bilan uglerod-uglerod aloqasini hosil qiladi. Organomagniy (Grignard reagentlari) va juda reaktiv va past kimyoselektivligi ma'lum bo'lgan organometalik reagentlar kabi yaxshi qo'llaniladigan organometalik reagentlarning o'ziga xos muammolari bilan taqqoslaganda, organosilikon birikmalari faol emas. [[Rux]], [[qalay]] va [[Bor (unsur)|bor]] kabi metallardan foydalanadigan boshqa metall organometalik reagentlar reaktivlik muammosini kamaytiradi, lekin har bir reagent bilan bog'liq boshqa muammolar mavjud. Organozink reagentlari namlikka sezgir, organotin birikmalari zaharli, [[Bororganik birikmalar|organobor]] reagentlari esa oson topilmaydi, qimmat va ko'pincha barqaror emas. Organosilanlar oson mavjud bo'lgan birikmalar bo'lib, ular ftorid yoki asosdan faollashganda (organotin yoki organobor birikmalari kabi) kimyoviy va regioselektiv tarzda CC aloqalarini hosil qilish uchun organogalidlar bilan reaksiyaga kirishishi mumkin. Birinchi xabar qilingan reaksiya palladiy katalizatori ishtirokida oson hosil bo'lgan (va faollashtirilgan) organosilikon nukleofillar va organogalidlarni (elektrofillar) ulash uchun ishlatilgan<ref name="Hiyama Discovery">{{jurnal manbasi|last=Hatanaka, Y.|last2=Hiyama, T.|journal=[[Journal of Organic Chemistry]]|title=Cross-coupling of organosilanes with organic halides mediated by a palladium catalyst and tris(diethylamino)sulfonium difluorotrimethylsilicate|year=1988|volume=53|issue=4|pages=918–920|doi=10.1021/jo00239a056}}</ref>. Ushbu kashfiyotdan beri turli guruhlar tomonidan ushbu reaksiya doirasini kengaytirish va organosilanning ftorid faollashuvi zarurati kabi ushbu birinchi birikma bilan bog'liq muammolarni "tuzatish" uchun ish olib borildi.
[[Fayl:Kumada_Silicate.svg|center|thumb|750x750px| Xiyama muftasini ishlab chiqish uchun silikat birikmasi pretsedenti<ref name="Kumada Fluorate">{{Citation|last=Yoshida, J.|last2=Tamao, K.|last3=Yamamoto, H.|last4=Kakui, T.|last5=Uchida, T.|last6=Kumada, M.|journal=[[Organometallics]]|title=Organofluorosilicates in organic synthesis. 14. Carbon-carbon bond formation promoted by palladium salts|year=1982|volume=1|issue=3|pages=542–549|doi=10.1021/om00063a025}}</ref>]]

== Reaksiya mexanizm ==
Organosilan [[Ftoridlar|ftorid]] (TBAF yoki TASF kabi tuzlar kabi) yoki asos bilan faollashtirilib, transmetalatsiya bosqichida C-Si aloqasining uzilishiga imkon beradigan darajada barqaror bo'lgan [[Valentlik|besh valentli]] kremniy markazini hosil qiladi<ref name="Hiyama miniaccount">{{Citation|last=Hiyama, T.|journal=[[Journal of Organometallic Chemistry]]|title=How I came across the silicon-based cross-coupling reaction|year=2002|volume=653|issue=1–2|pages=58–61|doi=10.1016/s0022-328x(02)01157-9}}</ref>. Ushbu asosiy oraliq mahsulotni shakllantirishning umumiy sxemasi quyida ko'rsatilgan. Bu bosqich in situ yoki reaksiyadagi katalitik aylanish bilan bir vaqtda sodir bo'ladi.
[[Fayl:Hiyama_intermediate.svg|center|750x750px]]
Xiyama bog'lanish mexanizmi katalitik siklni, shu jumladan A) oksidlovchi qo'shilish bosqichini kuzatib boradi, bunda organik galloid palladiyga qo'shiladi va metallni palladiydan (0) palladiyga (II) oksidlaydi; a B) transmetallanish bosqichi, bunda C-Si bog'i uziladi va ikkinchi uglerod bo'lagi palladiy markaziga bog'lanadi; va nihoyat C) reduktiv eliminatsiya bosqichi, bunda C-C bog'i hosil bo'ladi va palladiy tsiklni qaytadan boshlash uchun o'zining nol valentli holatiga qaytadi<ref name="Catalytic Cycle">{{Citation|author1-link=Norio Miyaura|author2-link=Akira Suzuki (chemist)|last=Miyaura, N.|last2=Suzuki, A.|journal=[[Chemical Reviews]]|title=Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds|year=1995|volume=95|issue=7|pages=2457–2483|doi=10.1021/cr00039a007}}</ref>. Katalitik sikl quyida ko'rsatilgan.
[[Fayl:Hiyama_Catalytic_Cycle.svg|center|678x678px| Hiyama ulanishining katalitik aylanishi]]

== Qo'llash doirasi va cheklovlari ==

=== Qo'llash doirasi ===
Xiyama birikmasi C<sub>sp</sub><small>2</small> -C<sub>sp</sub><small>2</small> (masalan, aril -aril) va C<sub>sp</sub><small>2</small> -C<sub>sp</sub><small>3</small> (masalan, aril- [[Toʻyingan uglevodorodlar|alkil]]) bog'larini hosil qilish uchun qo'llanilishi mumkin. Yaxshi sintetik rentabellik aril galogenidlar, vinilgalogenidlar va allilik galogenidlar va organo yodidlarning ulanishi bilan olinadi. Ushbu reaksiyaning doirasi Scott E. Daniya tomonidan o'rta o'lchamdagi halqalarni yopish uchun kengaytirildi<ref name="Ring Closing">{{Citation|last=Denmark, S. E.|last2=Yang, S.-M.|journal=[[Journal of the American Chemical Society]]|title=Intramolecular Silicon-Assisted Cross-Coupling Reactions: General Synthesis of Medium-Sized Rings Containing a 1,3-cis-cis Diene Unit|year=2002|volume=124|issue=10|pages=2102–2103|doi=10.1021/ja0178158|pmid=11878949}}</ref>.
[[Fayl:Hiyama_Ring_Closing.svg|alt=Hiyama coupling as a ring-closing reaction. Note, that there will be an 8 Carbonatom ring instead the shown 10-Carbon ring. (See the Paper)|left|thumb|750x750px| Hiyama ulanishi halqani yopish reaksiyasi sifatida<ref name="Ring Closing">{{Citation|last=Denmark, S. E.|last2=Yang, S.-M.|journal=[[Journal of the American Chemical Society]]|title=Intramolecular Silicon-Assisted Cross-Coupling Reactions: General Synthesis of Medium-Sized Rings Containing a 1,3-cis-cis Diene Unit|year=2002|volume=124|issue=10|pages=2102–2103|doi=10.1021/ja0178158|pmid=11878949}}</ref>]]
Alkilgalogenidlarni organo-galo-silanlar bilan muqobil organosilanlar sifatida ulash ham amalga oshirildi. Organoklorosilanlar aril yodidlarga qaraganda ko'p va odatda tejamkor bo'lgan arilxloridlar bilan bog'lanish imkonini beradi<ref name="Chlorosilanes">{{Citation|last=Gouda, K.-i.|last2=Hagiwara, E.|last3=Hatanaka, Y.|last4=Hiyama, T.|journal=[[The Journal of Organic Chemistry]]|title=Cross-Coupling Reactions of Aryl Chlorides with Organochlorosilanes: Highly Effective Methods for Arylation or Alkenylation of Aryl Chlorides|year=1996|volume=61|issue=21|pages=7232–7233|doi=10.1021/jo9611172|pmid=11667637}}</ref>. [[Nikel]] katalizatori GC Fu ''va boshqalar tomonidan xabar qilinganidek, organotrifluorosilanlarning yangi reaktivligiga kirish imkonini beradi''<ref name="Fu Nickel 1">{{Citation|last=Powell, D. A.|last2=Fu, G. C.|journal=[[Journal of the American Chemical Society]]|title=Nickel-Catalyzed Cross-Couplings of Organosilicon Reagents with Unactivated Secondary Alkyl Bromides|year=2004|volume=126|issue=25|pages=7788–7789|doi=10.1021/ja047433c|pmid=15212521}}</ref>. Ikkilamchi alkilgalogenidlar aril silanlar bilan birlashtiriladi<ref name="Fu Nickel 2">{{Citation|last=Strotman, N. A.|last2=Sommer, S.|last3=Fu, G. C.|journal=[[Angewandte Chemie International Edition]]|title=Hiyama Reactions of Activated and Unactivated Secondary Alkyl Halides Catalyzed by a Nickel/Norephedrine Complex|year=2007|volume=46|issue=19|pages=3556–3558|doi=10.1002/anie.200700440|pmid=17444579}}</ref>, bu reaksiya yordamida yaxshi hosil beradi.
[[Fayl:GC_Fu_Hiyama-coupling.svg|center|750x750px| Nikel-katalizli Hiyama muftasi GC Fu ''va boshqalar tomonidan kashf etilgan.'']]

=== Cheklovlar ===
Xiyama birikmasi organosilikon reagentini faollashtirish uchun ftoridga bo'lgan ehtiyoj bilan cheklangan. Ftorid qo'shilishi organik sintezda tez-tez ishlatiladigan kremniyni himoya qiluvchi guruhlarni (masalan, silil efirlarini<ref>Greene, T. W.; Wuts, P. G. M. Protective Groups In Organic Synthesis, 3rd ed.; 
John Wiley & Sons: New York, 1991. {{ISBN|0471160199}}</ref>) parchalaydi. Ftorid ioni ham asosiy hisoblanadi, shuning uchun asosiy sezgir himoya guruhlari, kislotali protonlar va funktsional guruhlar ushbu faollashtiruvchi qo'shilishi bilan ta'sir qilishi mumkin. Ushbu reaksiyaga oid faol tadqiqotlarning aksariyati ushbu muammoni chetlab o'tishni o'z ichiga oladi. Ushbu muammoni hal qilish uchun ko'plab guruhlar faollashtirish uchun boshqa asosiy qo'shimchalardan foydalanishni yoki boshqa organosilan reagentini birgalikda ishlatishni ko'rib chiqdilar, bu esa asl Hiyama ulanishining bir nechta o'zgarishiga olib keldi.

== Variantlar ==
Xiyama muftasining modifikatsiyalaridan biri silatsiklobutan halqasidan va quyida ko'rsatilganidek gidratlangan ftorid manbasidan foydalanadi<ref name="Denmark Cyclo">{{Citation|last=Denmark, S. E.|last2=Wehrli, D.|last3=Choi, J. Y.|journal=[[Organic Letters]]|title=Convergence of Mechanistic Pathways in the Palladium(0)-Catalyzed Cross-Coupling of Alkenylsilacyclobutanes and Alkenylsilanols|year=2000|volume=2|issue=16|pages=2491–2494|doi=10.1021/ol006170y|pmid=10956529}}</ref>. Bu alkilsilanni ishlatishdan ko'ra alkoksisilan/organosilanoldan foydalanishga taqlid qiladi. Ftorid manbasidan foydalangan holda bu reaksiya mexanizmi ftorid manbasidan foydalanishdan qochish mumkin bo'lgan kelajakdagi reaksiyalarni loyihalash imkonini berdi.
[[Fayl:Denmark_Cyclosilylbutane.svg|center|thumb|750x750px| Daniyaning silatsiklobutanlarning Xiyama birikmasining tavsiya etilgan o'tish holati<ref name="Denmark Cyclo">{{Citation|last=Denmark, S. E.|last2=Wehrli, D.|last3=Choi, J. Y.|journal=[[Organic Letters]]|title=Convergence of Mechanistic Pathways in the Palladium(0)-Catalyzed Cross-Coupling of Alkenylsilacyclobutanes and Alkenylsilanols|year=2000|volume=2|issue=16|pages=2491–2494|doi=10.1021/ol006170y|pmid=10956529}}</ref>]]

=== Ftoridsiz Xiyama muftalari ===
Xiyama muftasining ko'plab modifikatsiyalari ishlab chiqilgan bo'lib, ular ftorid faollashtiruvchisi/bazasidan foydalanishdan qochadi. Organoklorosilanlardan foydalangan holda, Xiyama asosiy faollashtiruvchi sifatida [[Natriy gidroksid|NaOH]] dan foydalangan holda ulanish sxemasini topdi<ref name="Hiyama Hydroxide">{{Citation|last=Hagiwara, E.|last2=Gouda, K.-i.|last3=Hatanaka, Y.|last4=Hiyama, T.|journal=[[Tetrahedron Letters]]|title=NaOH-Promoted cross-coupling reactions of organosilicon compounds with organic halides: Practical routes to biaryls, alkenylarenes and conjugated dienes|year=1997|volume=38|issue=3|pages=439–442|doi=10.1016/s0040-4039(96)02320-9}}</ref>. NaOH<ref name="Alkoxy silane">{{Citation|last=Shi, S.|last2=Zhang, Y.|journal=[[The Journal of Organic Chemistry]]|title=Pd(OAc)2-Catalyzed Fluoride-Free Cross-Coupling Reactions of Arylsiloxanes with Aryl Bromides in Aqueous Medium|year=2007|volume=72|issue=15|pages=5927–5930|doi=10.1021/jo070855v|pmid=17585827}}</ref> va hatto suv kabi yumshoqroq asoslardan foydalangan holda alkoksisilanlardan foydalangan holda o'zgarishlar haqida xabar berilgan<ref name="Wolf">{{Citation|last=Wolf, C.|last2=Lerebours, R.|journal=[[Organic Letters]]|title=Palladium−Phosphinous Acid-Catalyzed NaOH-Promoted Cross-Coupling Reactions of Arylsiloxanes with Aryl Chlorides and Bromides in Water|year=2004|volume=6|issue=7|pages=1147–1150|doi=10.1021/ol049851s|pmid=15040744}}</ref>. Ushbu mexanizmlarni o'rganish organosilanollarni ulash sheriklari sifatida ishlatadigan Xiyama-Daniya bog'lanishining rivojlanishiga olib keldi.<nowiki></br></nowiki>
[[Fayl:Hiyama_NaOH.svg|center|thumb|750x750px| NaOH tomonidan targ'ib qilingan Xiyama muftasi<ref name="Hiyama Hydroxide">{{Citation|last=Hagiwara, E.|last2=Gouda, K.-i.|last3=Hatanaka, Y.|last4=Hiyama, T.|journal=[[Tetrahedron Letters]]|title=NaOH-Promoted cross-coupling reactions of organosilicon compounds with organic halides: Practical routes to biaryls, alkenylarenes and conjugated dienes|year=1997|volume=38|issue=3|pages=439–442|doi=10.1016/s0040-4039(96)02320-9}}</ref>]]


Ftoridsiz Xiyama muftalarining yana bir klassi Lyuis kislotasi qo'shimchasidan foydalanishni o'z ichiga oladi, bu K <nowiki><small id="mwnw">3</small></nowiki> PO <nowiki><small id="mwoA">4</small></nowiki><ref name="Hiyama Milder">{{Citation|last=Nakao, Y.|last2=Takeda, M.|last3=Matsumoto, T.|last4=Hiyama, T.|journal=[[Angewandte Chemie]]|title=Cross-Coupling Reactions through the Intramolecular Activation of Alkyl(triorgano)silanes|year=2010|volume=122|issue=26|pages=4549–4552|doi=10.1002/ange.201000816|bibcode=2010AngCh.122.4549N}}</ref> kabi asoslardan foydalanishga yoki reaksiyani asosiy qo'shimchasiz davom ettirishga imkon beradi<ref name="Hiyama Silver">{{Citation|last=Hirabayashi, K.|last2=Mori, A.|last3=Kawashima, J.|last4=Suguro, M.|last5=Nishihara, Y.|last6=Hiyama, T.|journal=[[The Journal of Organic Chemistry]]|title=Palladium-Catalyzed Cross-Coupling of Silanols, Silanediols, and Silanetriols Promoted by Silver(I) Oxide|year=2000|volume=65|issue=17|pages=5342–5349|doi=10.1021/jo000679p|pmid=10993364}}</ref><ref name="Hiyama Alkyne">{{Citation|last=Nishihara, Y.|last2=Ikegashira, K.|last3=Hirabayashi, K.|last4=Ando, J.-i.|last5=Mori, A.|last6=Hiyama, T.|journal=[[The Journal of Organic Chemistry]]|title=Coupling Reactions of Alkynylsilanes Mediated by a Cu(I) Salt: Novel Syntheses of Conjugate Diynes and Disubstituted Ethynes|year=2000|volume=65|issue=6|pages=1780–1787|doi=10.1021/jo991686k|pmid=10814151}}</ref>. [[Mis]] ko-katalizatorining qo'shilishi, shuningdek, yumshoqroq faollashtiruvchi vositadan<ref name="Hiyama Milder" /> foydalanishga imkon berishi va hatto katalitikda palladiy (II) va mis (I) aylanmasini olishi ko'rsatilgan. stexiometrik Lyuis kislotasini qo'shishdan ko'ra tsikl (masalan, kumush (I)<ref name="Hiyama Silver" />, mis (I)<ref name="Hiyama Alkyne" />).
[[Fayl:Hiyama_Copper.svg|center|thumb|750x750px| Mis ko-katalizator bilan Xiyama ulanishi<ref name="Hiyama Milder">{{Citation|last=Nakao, Y.|last2=Takeda, M.|last3=Matsumoto, T.|last4=Hiyama, T.|journal=[[Angewandte Chemie]]|title=Cross-Coupling Reactions through the Intramolecular Activation of Alkyl(triorgano)silanes|year=2010|volume=122|issue=26|pages=4549–4552|doi=10.1002/ange.201000816|bibcode=2010AngCh.122.4549N}}</ref>]]

=== Hiyama-Daniya birikmasi ===
 
'''Hiyama-Daniya muftasi ning modifikatsiyasi Hiyama muftasi bu organosilanollar va organik galogenidlarni biriktiruvchi''' sherik sifatida ishlatish uchun ftorli qo'shimchani talab qilmaydi. Umumiy reaksiya sxemasi quyida keltirilgan bo'lib, unda br / ' Nsted bazasini aktivlovchi modda sifatida ftoriddan farqli o'laroq, [[Fosfororganik birikmalar|metall markazida fosfin ligandlar]] ham ishlatiladi<ref name="Denmark Review">{{jurnal manbasi|last=Denmark, S. E.|last2=Regens, C. S.|journal=[[Accounts of Chemical Research]]|title=Palladium-Catalyzed Cross-Coupling Reactions of Organosilanols and Their Salts: Practical Alternatives to Boron- and Tin-Based Methods|url=https://archive.org/details/sim_accounts-of-chemical-research_2008-11_41_11/page/1486|year=2008|volume=41|issue=11|pages=1486–1499|doi=10.1021/ar800037p|pmid=18681465|pmc=2648401}}</ref>.
[[Fayl:Hiyama-Denmark_General.svg|center|500x500px| Xiyama-Daniya ulanishining umumiy sxemasi]]
Ushbu reaksiyaning o'ziga xos misoli reagentlar bilan ko'rsatilgan. Agar asl Hiyama protokolida bo'lgani kabi ftorid ishlatilsa, ''tert'' -butildimetilsilil (TBS) efiri yo'q qilingan bo'lar edi<ref name="Denmark Paper">{{Citation|last=Denmark, S. E.|last2=Smith, R. C.|last3=Chang, W.-T. T.|last4=Muhuhi, J. M.|journal=[[Journal of the American Chemical Society]]|title=Cross-Coupling Reactions of Aromatic and Heteroaromatic Silanolates with Aromatic and Heteroaromatic Halides|year=2009|volume=131|issue=8|pages=3104–3118|doi=10.1021/ja8091449|pmid=19199785|pmc=2765516}}</ref>.
[[Fayl:Hiyama-Denmark_Coupling_Example_with_(-OTBS).png|center|thumb|750x750px| Ftorid qo'shimchalarisiz silanolni ulash misoli<ref name="Denmark Paper">{{Citation|last=Denmark, S. E.|last2=Smith, R. C.|last3=Chang, W.-T. T.|last4=Muhuhi, J. M.|journal=[[Journal of the American Chemical Society]]|title=Cross-Coupling Reactions of Aromatic and Heteroaromatic Silanolates with Aromatic and Heteroaromatic Halides|year=2009|volume=131|issue=8|pages=3104–3118|doi=10.1021/ja8091449|pmid=19199785|pmc=2765516}}</ref>]]

==== Xiyama-Daniya ulanish mexanizmi ====
Ushbu reaksiya mexanizmini o'rganish shuni ko'rsatadiki, silonat hosil bo'lishi palladiy markaziga organosilan qo'shilishini faollashtirish uchun zarur bo'lgan narsadir. Pentavalent kremniyning mavjudligi shart emas va [[Kimyoviy kinetika|kinetik]] tahlil shuni ko'rsatdiki, bu reaksiya silonat konsentratsiyasiga birinchi darajali bog'liqdir<ref name="Denmark Review">{{jurnal manbasi|last=Denmark, S. E.|last2=Regens, C. S.|journal=[[Accounts of Chemical Research]]|title=Palladium-Catalyzed Cross-Coupling Reactions of Organosilanols and Their Salts: Practical Alternatives to Boron- and Tin-Based Methods|url=https://archive.org/details/sim_accounts-of-chemical-research_2008-11_41_11/page/1486|year=2008|volume=41|issue=11|pages=1486–1499|doi=10.1021/ar800037p|pmid=18681465|pmc=2648401}}</ref>. Buning sababi, transmetalatsiya bosqichida Pd-O aloqasi hosil bo'lgan asosiy bog'lanish, keyin uglerod bo'lagini palladiy markaziga o'tkazish imkonini beradi. Ushbu kuzatuvga asoslanib, ushbu katalitik tsikldagi tezlikni cheklovchi bosqich Pd-O bog'lanishi bo'lib, unda silonat kontsentratsiyasining ortishi bu reaksiya tezligini oshiradi (tezroq reaksiyalardan dalolat beradi).
[[Fayl:Hiyama-Denmark_Cycle_Equation.svg|center|750x750px]]
[[Fayl:Hiyama-Denmark_Cat._Cycle.svg|center|500x500px| Xiyama-Daniya birikmasining katalitik aylanishi]]

== Yana qarang ==

* [[Xush reaksiya]]
* [[Kumada ulanishi]]
* [[Negishi ulanishi]]
* [[Sonogashira ulanishi]]
* [[Harakatsiz reaksiya]]
* [[Suzuki reaksiyasi]]
* [[Palladiy bilan katalizlangan ulanish reaksiyalari]]

== Havolalar ==

* [https://www.organic-chemistry.org/namedreactions/hiyama-coupling.shtm Hiyama muftalari haqida ma'lumot]
* [https://www.organic-chemistry.org/namedreactions/hiyama-denmark-coupling.shtm Hiyama-Daniya muftalari haqida ma'lumot].

== Manbalar ==
{{manbalar}}

[[Turkum:Palladiy]]
[[Turkum:Organo metallar kimyosi]]
[[Turkum:Pages with unreviewed translations]]